Flynn & Friends started in January, 1986 when Mitch Flynn mailed out a series of creatively enhanced pencils to 500 people in Western New York, in the process winning the Best of Show award from the Professional Communicators of Western New York. This was the first in a series of three-dimensional direct mail campaigns which has become a trademark of the agency under the name Chunk Mail®.

In 1987, F&F doubled when Ellen Goldstein became the first "friend" (an appropriate title, as Mitch and Ellen are husband and wife.) In 1988, Mitch met Marc Adler in the latter's capacity as marketing director for Flynn & Friends' client KVS Information Systems. In 1990, Mitch met Barb Keough as a student in his class in Communication Design at the University at Buffalo.

In 1993, Barb and Marc joined the agency as, respectively, Communications Coordinator and Director of New Business Development. In December, 2001, Marc was named Vice President of Client Services. In May, 2003, Barb was named Vice President of Operations.

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